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Orotic acid information


Orotic acid
Clinical data
Other namesuracil-6-carboxylic acid
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
IUPAC name
  • 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
CAS Number
  • 65-86-1 checkY
PubChem CID
  • 967
IUPHAR/BPS
  • 4690
DrugBank
  • DB02262 ☒N
ChemSpider
  • 942 ☒N
UNII
  • 61H4T033E5
KEGG
  • C00295 ☒N
CompTox Dashboard (EPA)
  • DTXSID0025814 Edit this at Wikidata
ECHA InfoCard100.000.563 Edit this at Wikidata
Chemical and physical data
FormulaC5H4N2O4
Molar mass156.097 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(O)\C1=C\C(=O)NC(=O)N1
InChI
  • InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) ☒N
  • Key:PXQPEWDEAKTCGB-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Orotic acid (/ɔːˈrɒtɪk/)[1] is a pyrimidinedione and a carboxylic acid. Historically, it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin.

The compound is synthesized in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase[2] or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate.

  1. ^ "Orotic acid". Merriam-Webster.com Dictionary. Retrieved 2023-02-07.
  2. ^ Rawls J, Knecht W, Diekert K, Lill R, Löffler M (April 2000). "Requirements for the mitochondrial import and localization of dihydroorotate dehydrogenase". European Journal of Biochemistry. 267 (7): 2079–2087. doi:10.1046/j.1432-1327.2000.01213.x. PMID 10727948.

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Orotic acid

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Orotic acid (/ɔːˈrɒtɪk/) is a pyrimidinedione and a carboxylic acid. Historically, it was believed to be part of the vitamin B complex and was called...

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Orotic aciduria

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synthesis pathway. Orotic aciduria is characterized by excessive excretion of orotic acid in urine because of the inability to convert orotic acid to UMP. It...

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Nucleic acid metabolism

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synthesis can lead to the genetic disease Orotic aciduria which causes excessive excretion of orotic acid in the urine. Nucleotides are initially made...

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Orotate phosphoribosyltransferase

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Orotate phosphoribosyltransferase (OPRTase) or orotic acid phosphoribosyltransferase is an enzyme involved in pyrimidine biosynthesis. It catalyzes the...

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Magnesium orotate

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Magnesium orotate, the magnesium salt of orotic acid, is a mineral supplement. It can be used in treating extracellular magnesium deficiency, as well...

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Blood urea nitrogen

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pattern. OTC deficiency is also accompanied by hyperammonemia and high orotic acid levels. BUN is usually reported in mg/dL in some countries (e.g. United...

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Ornithine transcarbamylase deficiency

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block is proximal to these intermediates) and increased orotic acid. The increased orotic acid concentrations result from the buildup of carbamoyl phosphate...

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Lithium orotate

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Lithium orotate (C5H3LiN2O4) is a salt of orotic acid and lithium. It is available as the monohydrate, LiC5H3N2O4·H2O. In this compound, lithium is non-covalently...

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Nucleotide

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carbamoyl-phosphate in the cytoplasm to the common precursor ring structure orotic acid, onto which a phosphorylated ribosyl unit is covalently linked. Purines...

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Uridine monophosphate

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result in orotic aciduria, a metabolic disorder. In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were...

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Pyrimidine

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1879, when Grimaux reported the preparation of barbituric acid from urea and malonic acid in the presence of phosphorus oxychloride. The systematic study...

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Ornithine transcarbamylase

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uridine monophosphate synthetic pathway. Orotic acid is a product of this pathway. Increased levels of orotic acid in urine can be an indicator that a patient...

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Selectable marker

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lacking orotidine-5'-phosphate decarboxylase activity in yeast: 5-fluoro-orotic acid resistance". Mol. Gen. Genet. 197 (2): 345–6. doi:10.1007/bf00330984...

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List of chemical compounds with unusual names

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2013. Retrieved 4 November 2013. Chester, DO (1979). "Three New Aliphatic Acids from Lichens of Genus Parmelia (Subgenus Xanthoparmelia )". Australian Journal...

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B vitamins

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folate ("pteroylmonoglutamic acid" in this nomenclature). Vitamin B13: orotic acid. Vitamin B14: cell proliferant, anti-anemia, rat growth factor, and antitumor...

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Dihydroorotate dehydrogenase

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5-Dihydroorotic acid Orotic acid. Note the double bond in the ring. The particular mechanism for the dehydrogenation of dihydroorotic acid by DHODH differs...

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B13

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of chess Moseley, a suburb of Birmingham, England, from its postcode Orotic acid, formerly known as Vitamin B13 Boron-13 (B-13 or 13B), an isotope of...

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Dihydroorotase

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"Enzymatic synthesis and breakdown of a pyrimidine, orotic acid. I. Dihydroortic acid, ureidosuccinic acid, and 5-carboxymethylhydantoin" (PDF). The Journal...

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Orotidine

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Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a β-N1-glycosidic bond. It is found in bacteria, fungi and plants. It was...

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Uridine monophosphate synthase

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PMID 2767686. Traut TW, Jones ME (1996). Uracil metabolism--UMP synthesis from orotic acid or uridine and conversion of uracil to beta-alanine: enzymes and cDNAs...

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List of compounds with carbon number 5

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C5H4N2O pyrazinecarboxaldehyde 5780-66-5 C5H4N2O2 pyrazinoic acid 98-97-5 C5H4N2O4 orotic acid 65-86-1 C5H4N4 pyridotetrazole 274-87-3 C5H4N4O allopurinol...

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Isothermal microcalorimetry

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effective in accomplishing enzymatic assays for orotic acid in milk (Anastasi et al. 2000) and malic acid in fruits, wines and other beverages and also...

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Argininemia

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the presence of the condition: Plasma ammonia concentration. Urinary orotic acid concentration Red blood cell arginase enzyme activity (measurement) The...

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Megaloblastic anemia

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Inherited Pyrimidine Synthesis Disorders: Orotic aciduria Inherited DNA Synthesis Disorders Toxins and Drugs: Folic acid antagonists (methotrexate) Purine synthesis...

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Ureidosuccinase

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KORNBERG A (1955). "Enzymatic synthesis and breakdown of a pyrimidine, orotic acid. III Ureidosuccinase". J. Biol. Chem. 212 (2): 909–20. PMID 14353892...

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Carboxymethylhydantoinase

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"Enzymatic synthesis and breakdown of a pyrimidine, orotic acid. I Dihydroortic acid, ureidosuccinic acid, and 5-carboxymethylhydantoin". J. Biol. Chem. 207...

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